title: Cyanuric chloride/sodium borohydride: a new reagent combination for reductive opening of 4,6-benzylidene acetals of carbohydrates to primary alcohols.
abstract: In the first such example, NaBH4 in combination with cyanuric chloride (TCT) has been used to obtain 6-hydroxy-4-benzyl ether derivatives from 4,6-benzylidene acetals of carbohydrates. The nature of hydride donor determines the regioselectivity of acetal opening. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process, inexpensive reagents and wide application mark the benefits of the newly developed reagent system.
authors.affiliation: Academy of Scientific and Innovative Research, Jammu, India; CSIR-IIIM Jammu Natural Product Chemistry Division, Jammu, India.
authors.forename: Madhubabu
authors.initials: M
authors.lastname: Tatina
authors.forename: Syed Khalid
authors.initials: SK
authors.lastname: Yousuf
authors.forename: Subrayashastry
authors.initials: S
authors.lastname: Aravinda
authors.forename: Baldev
authors.initials: B
authors.lastname: Singh
authors.forename: Debaraj
authors.initials: D
authors.lastname: Mukherjee
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014227:Triazines / Q000737:chemistry*
chemical_list: D000080:Acetals; D000438:Alcohols; D001894:Borohydrides; D002241:Carbohydrates; D014227:Triazines; C019309:cyanuric chloride; C025364:sodium borohydride
keywords: Benzylidene derivative reductive opening; Primary OH; Sodium borohydride; TCT